TWI668222B - 5型磷酸二酯酶抑制劑的甲磺酸鹽多晶物及其製備方法和應用 - Google Patents

5型磷酸二酯酶抑制劑的甲磺酸鹽多晶物及其製備方法和應用 Download PDF

Info

Publication number: TWI668222B
Authority: TW; Taiwan
Prior art keywords: type; phosphodiesterase; inhibitor; polymorph; phosphodiesterase inhibitor
Prior art date: 2017-05-19

Application number

TW107116187A

Other languages

English (en)

Chinese (zh)

Other versions

TW201900646A (zh

Inventor

王靖林

于瑞梅

廉瓊瓊

Original Assignee

王靖林

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2017-05-19

Filing date

2018-05-11

Publication date

2019-08-11

2018-05-11 Application filed by 王靖林 filed Critical 王靖林

2019-01-01 Publication of TW201900646A publication Critical patent/TW201900646A/zh

2019-08-11 Application granted granted Critical

2019-08-11 Publication of TWI668222B publication Critical patent/TWI668222B/zh

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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title claims abstract description 77
229940099471 Phosphodiesterase inhibitor Drugs 0.000 title claims abstract description 39
239000002571 phosphodiesterase inhibitor Substances 0.000 title claims abstract description 39
238000002360 preparation method Methods 0.000 title claims description 40
239000003814 drug Substances 0.000 claims abstract description 24
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
239000011343 solid material Substances 0.000 claims description 12
239000013078 crystal Substances 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
229940098779 methanesulfonic acid Drugs 0.000 claims description 10
229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
239000000706 filtrate Substances 0.000 claims description 9
239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 9
238000003756 stirring Methods 0.000 claims description 9
208000010228 Erectile Dysfunction Diseases 0.000 claims description 7
201000001881 impotence Diseases 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 6
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 6
238000000967 suction filtration Methods 0.000 claims description 6
102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 5
108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
238000002425 crystallisation Methods 0.000 claims description 4
230000008025 crystallization Effects 0.000 claims description 4
239000005457 ice water Substances 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 3
206010002383 Angina Pectoris Diseases 0.000 claims description 3
206010003210 Arteriosclerosis Diseases 0.000 claims description 3
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
206010005060 Bladder obstruction Diseases 0.000 claims description 3
206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
206010057671 Female sexual dysfunction Diseases 0.000 claims description 3
206010019280 Heart failures Diseases 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
206010021639 Incontinence Diseases 0.000 claims description 3
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
208000006011 Stroke Diseases 0.000 claims description 3
206010001053 acute respiratory failure Diseases 0.000 claims description 3
208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
206010006451 bronchitis Diseases 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
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206010057672 Male sexual dysfunction Diseases 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
230000006806 disease prevention Effects 0.000 claims 2
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 claims 1
230000004064 dysfunction Effects 0.000 claims 1
150000004702 methyl esters Chemical class 0.000 claims 1
238000001556 precipitation Methods 0.000 claims 1
230000003068 static effect Effects 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
238000010792 warming Methods 0.000 claims 1
229940079593 drug Drugs 0.000 abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
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210000004369 blood Anatomy 0.000 description 15
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BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 14
238000003304 gavage Methods 0.000 description 8
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238000002329 infrared spectrum Methods 0.000 description 5
238000000113 differential scanning calorimetry Methods 0.000 description 4
229960003310 sildenafil Drugs 0.000 description 4
-1 5-[2-ethoxy-5-(4-methylpyrazin-1-ylthiocarbonyl)phenyl ]-1-Methyl-3-n-propyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidine-7-thione mesylate Chemical compound 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002250 absorbent Substances 0.000 description 2
230000002745 absorbent Effects 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
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238000011208 chromatographic data Methods 0.000 description 2
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239000003085 diluting agent Substances 0.000 description 2
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238000010828 elution Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
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239000003205 fragrance Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
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238000006467 substitution reaction Methods 0.000 description 2
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238000010189 synthetic method Methods 0.000 description 2
238000002076 thermal analysis method Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
0 CC(CC*(C1NC2C(C=C(CC3)C(N4CCN(C)CC4)=S)=C3*22)C2=S)*C1C=C Chemical compound CC(CC*(C1NC2C(C=C(CC3)C(N4CCN(C)CC4)=S)=C3*22)C2=S)*C1C=C 0.000 description 1
229910002483 Cu Ka Inorganic materials 0.000 description 1
101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 description 1
101150098694 PDE5A gene Proteins 0.000 description 1
SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 description 1
239000003655 absorption accelerator Substances 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000010100 anticoagulation Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000036267 drug metabolism Effects 0.000 description 1
229940088679 drug related substance Drugs 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
239000002329 esterase inhibitor Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
229960001008 heparin sodium Drugs 0.000 description 1
238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
MIJFNYMSCFYZNY-UHFFFAOYSA-N mirodenafil Chemical compound C1=C(C=2NC=3C(CCC)=CN(CC)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 MIJFNYMSCFYZNY-UHFFFAOYSA-N 0.000 description 1
229950002245 mirodenafil Drugs 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
BRFMYUCUGXFMIO-UHFFFAOYSA-N phosphono dihydrogen phosphate phosphoric acid Chemical compound OP(O)(O)=O.OP(O)(=O)OP(O)(O)=O BRFMYUCUGXFMIO-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
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208000024891 symptom Diseases 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
WOXKDUGGOYFFRN-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 WOXKDUGGOYFFRN-IIBYNOLFSA-N 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
IYFNEFQTYQPVOC-UHFFFAOYSA-N udenafil Chemical compound C1=C(C=2NC=3C(CCC)=NN(C)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)NCCC1CCCN1C IYFNEFQTYQPVOC-UHFFFAOYSA-N 0.000 description 1
229960000438 udenafil Drugs 0.000 description 1
229960002381 vardenafil Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/04—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing only one sulfo group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

TW107116187A 2017-05-19 2018-05-11 5型磷酸二酯酶抑制劑的甲磺酸鹽多晶物及其製備方法和應用 TWI668222B (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CN201710361203.7A CN107141294B (zh)	2017-05-19	2017-05-19	一种5型磷酸二酯酶抑制剂的甲磺酸盐多晶物及其制备方法和应用
??201710361203.7		2017-05-19

Publications (2)

Publication Number	Publication Date
TW201900646A TW201900646A (zh)	2019-01-01
TWI668222B true TWI668222B (zh)	2019-08-11

Family

ID=59777648

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TW107116187A TWI668222B (zh)	2017-05-19	2018-05-11	5型磷酸二酯酶抑制劑的甲磺酸鹽多晶物及其製備方法和應用

Country Status (7)

Country	Link
US (1)	US10654859B2 (fr)
EP (1)	EP3553060B1 (fr)
CN (1)	CN107141294B (fr)
ES (1)	ES2852148T3 (fr)
PL (1)	PL3553060T3 (fr)
TW (1)	TWI668222B (fr)
WO (1)	WO2018209809A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111732593A (zh) *	2020-07-07	2020-10-02	黄泳华	哌嗪氧化物衍生物及其组合物、制备方法与用途
CN113603692B (zh) *	2021-06-24	2022-11-04	济南美鲁威生物科技有限公司	5型磷酸二酯酶抑制剂的多晶物及其制备方法和应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1240134A (zh) *	1998-06-22	2000-01-05	辉瑞研究及发展公司	治疗性障碍的鼻内给药制剂
CN104650093A (zh) *	2015-02-02	2015-05-27	王靖林	一种西地那非类似物的合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20060035905A1 (en) *	2004-02-06	2006-02-16	Becton, Dickinson And Company	Formulations of phosphodiesterase 5 inhibitors and methods of use
CN101343275A (zh)	2008-07-29	2009-01-14	段波	吡唑并嘧啶硫酮类和其盐的制备及治疗男性勃起功能障碍的应用

2017
- 2017-05-19 CN CN201710361203.7A patent/CN107141294B/zh active Active
- 2017-07-26 PL PL17909843T patent/PL3553060T3/pl unknown
- 2017-07-26 EP EP17909843.9A patent/EP3553060B1/fr active Active
- 2017-07-26 WO PCT/CN2017/094467 patent/WO2018209809A1/fr not_active Ceased
- 2017-07-26 US US16/317,208 patent/US10654859B2/en active Active
- 2017-07-26 ES ES17909843T patent/ES2852148T3/es active Active
2018
- 2018-05-11 TW TW107116187A patent/TWI668222B/zh active

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1240134A (zh) *	1998-06-22	2000-01-05	辉瑞研究及发展公司	治疗性障碍的鼻内给药制剂
CN104650093A (zh) *	2015-02-02	2015-05-27	王靖林	一种西地那非类似物的合成方法

Also Published As

Publication number	Publication date
EP3553060B1 (fr)	2020-12-23
WO2018209809A1 (fr)	2018-11-22
ES2852148T3 (es)	2021-09-13
US20190292192A1 (en)	2019-09-26
EP3553060A4 (fr)	2019-11-20
PL3553060T3 (pl)	2021-06-14
TW201900646A (zh)	2019-01-01
EP3553060A1 (fr)	2019-10-16
CN107141294B (zh)	2018-04-17
CN107141294A (zh)	2017-09-08
US10654859B2 (en)	2020-05-19

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